Not the top quality/selection of food, but Brant House offers $2 beverages and half priced appetizers on Fridays until 8. I believe the same offer exists on Thursdays until around 9, if I'm not mistaken. Can't beat toonie drinks! :)

I have fond memories of sitting at little bars, terraces and patios in Marseille, Aix-en-Provence, Avignon (etc) and getting tapas style foods whenever we would order a round of drinks in the evenings. It was great, and I wish I could find somewhere here that did the same thing.

I went to Paupers Pub at 539 Bloor West once for Happy Hour, and it was quite nice. It was 1/2 price appetizers, with a big variety and selection. We tried the flatbread bruschetta, roaster wings and fries. No complaints but that the wings were a little bit too dry.. Madison Pub (its sister pub) also has that Happy Hour special.